Abstract
A novel glycosyl donor with a triisopropylsilyl (TIPS) nonparticipating group at O-2 is introduced for use in 1,2-cis-galactosylation. Coupling the 2-O-TIPS-substituted thiogalactoside donor with a series of mono- and disaccharide glycosyl acceptors was found to lead exclusively to α-linked oligosaccharides. The observed exceptionally high α-selectivity was interpreted in terms of conformational changes in the glycosyl cation induced by the bulky 2-O-TIPS group.
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